An Alternative Synthesis of (+)-Biotin from Carbohydrate, a Formal Synthesis of (+)-Biotin fromd-Glucosamine

Biotin: A Timeless Challenge for Total Synthesis

“…Subsequent to this work, the Ohrui group developed a shorter sequence to the same diol 80 that took advantage of the correct absolute configuration of the amino group in d -glucosamine that will eventually appear at C-4 in (+)-biotin (Scheme ) …”

“…Subsequent to this work, the Ohrui group developed a shorter sequence to the same diol 80 that took advantage of the correct absolute configuration of the amino group in D-glucosamine that will eventually appear at C-4 in (+)-biotin (Scheme 27). 53 Worthy of note here is the use of a benzyloxycarbonyl group as reactive amine protecting group to form the imidazolidinone ring upon treatment of 83 with sodium hydride.…”

NMR studies on chiral intermediates in the total synthesis of (+)‐biotin from D‐mannose

“…1) has attracted considerable attention due to its importance in human nutrition and animal health 1–3. Since the first total synthesis of 1 was accomplished about 57 years ago, a continuous endeavor has now resulted in a great variety of synthetic approaches,4–10 among them, chiral pool strategy using carbohydrates as starting material was one of the most attractive approaches. Recently, a novel enantiospecific approach to this vitamin, which has taken advantage of some chiral information stored in D ‐mannose via 12 chiral intermediates, has been developed in our research group (Fig.…”

The Behavior of Some 2-Acetamido-2-deoxy-furanoses in the Presence of Alkaline Ion-exchange Resin

“…Acetylation of 3 (150 mg) with acetic anhydride (1 ml) in pyridine (3 ml) 'at O°C gave the product. It was purified by chromatography on a column of silica gel (15 g (6). Acetylation of 5 (150 mg) was performed in the same way as described above.…”

“…These isopropylidene derivatives are effective to synthesize biologically active compounds. For example, Prumycin,4) (+ )-biotin 6 ) and some analogs7) of N-acetylmuramoyl-L-alanyl-Disoglutamine were synthesized from benzyl 2-(benzyloxycarbonylamino)-2-deoxy-5,6-0-isopropylidene-!3-D-gluc<;lfuranoside.…”